Ethanol → HCID 69071952, compound

HRID 1870040Notes

Reaction equation

HRID 1870040 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](OS(C(F)(F)F)(=O)=O)=[CH:18][CH2:17][C:16]([CH3:32])([CH3:31])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:33].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:66]=[O:67].[CH2:69]([OH:71])[CH3:70]>CCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:69]([O:71][C:66]([C:19]1[C:20]2[C:15](=[CH:14][C:13]([C:12]#[C:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:34])=[C:6]([F:33])[CH:7]=3)=[CH:22][CH:21]=2)[C:16]([CH3:31])([CH3:32])[CH2:17][CH:18]=1)=[O:67])[CH3:70]

Participants

9

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 58883468HCID 58883468, compound2×

Product 1

HCID 69071952HCID 69071952, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure E and using [4-(8,8-dimethyl-5-trifluoromethanesulfonyloxy-7,8-dihydro-naphthalen-2-ylethynyl)-2-fluoro-phenyl]-acetic acid methyl ester (Intermediate 203, 0.32 g, 0.65 mmol), palladium acetate (0.015 g, 0.064 mmol), 1,3-bis(diphenylphosphino)propane (0.027 g, 0.064 mmol), N,N-dimethylformamide (5 mL), ethanol (2 mL) and triethyl amine (2 mL) followed by flash column chromatography over silica gel (230-400 mesh) using 5-15% ethyl acetate in hexane as the eluent the title compound was obtained (0.15 g, 55%) as a yellow oil.

Sources & evidence

ORD record
ord-895f54e511144fe985f728305b1ee50b
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

Loading…